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A highly efficient alkenylation reaction of arylglyoxals with 3-vinylindoles catalyzed by chiral calcium phosphate is described. Structurally diverse allylic alcohols bearing indole and carbonyl units are prepared in excellent yields, good diastereoselectivities, and high to excellent enantioselectivities. These products are good building blocks for the synthesis of polysubstituted chiral tetrahydrocarbozol-2-ones. The mechanism study indicates that the most likely role of the catalyst is to activate the hydrate of arylglyoxal and control the stereoselectivity via desymmetric coordination.

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Nitrogen-containing 4-alkoxybenzaldehyde analogues as a kind of water-soluble aldehyde are important intermediates for small molecule anticancer drugs. A rapid and high yield synthetic method for nitrogen-containing 4alkoxybenzaldehyde analogues was established in this work. The target compound was synthesized from the commercially available 4-alkoxybenzaldehyde through two steps nucleophilic substitution. The structure of the target product was confirmed by 1 HNMR and MS. In addition, the synthetic method was optimized. The total yield of the two steps was high up to 99%.